JPH04288031A - Polyallyl compound - Google Patents
Polyallyl compoundInfo
- Publication number
- JPH04288031A JPH04288031A JP4970491A JP4970491A JPH04288031A JP H04288031 A JPH04288031 A JP H04288031A JP 4970491 A JP4970491 A JP 4970491A JP 4970491 A JP4970491 A JP 4970491A JP H04288031 A JPH04288031 A JP H04288031A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyphenyl
- bis
- diallyl
- sulfone
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 150000003457 sulfones Chemical class 0.000 abstract description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 3
- MTMKZABGIQJAEX-UHFFFAOYSA-N 4,4'-sulfonylbis[2-(prop-2-en-1-yl)phenol] Chemical compound C1=C(CC=C)C(O)=CC=C1S(=O)(=O)C1=CC=C(O)C(CC=C)=C1 MTMKZABGIQJAEX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004593 Epoxy Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000006698 induction Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、硬化型樹脂原料及び、
エポキシ樹脂原料として有用なポリアリル型化合物に関
する。[Industrial Application Field] The present invention relates to a curable resin raw material and
This invention relates to polyallyl type compounds useful as raw materials for epoxy resins.
【０００２】0002
【従来の技術】従来ポリアリル化合物が、種々の用途に
架橋剤として検討なされてきた。たとえば、多種の骨格
について多官能化などの検討がされているが、従来主に
検討されてきたのは、多塩基酸のポリグリシジルエーテ
ル、ポリアリルエーテルなどの、エーテル結合やエステ
ル結合などをもつもので、酸やアルカリに対して抵抗力
が小さかった。要求が厳しいＩＣの封止剤などでの使用
には更に改善する必要があった。BACKGROUND OF THE INVENTION Conventionally, polyallyl compounds have been investigated as crosslinking agents for various uses. For example, studies have been conducted on the multifunctionalization of various types of skeletons, but the ones that have been mainly studied so far have been polybasic acids such as polyglycidyl ethers and polyallyl ethers, which have ether bonds and ester bonds. It has low resistance to acids and alkalis. Further improvements were needed for use in demanding IC encapsulants.
【０００３】0003
【発明が解決しようとする課題】本発明は、単位重量当
たりの官能基密度が高く、良好な硬化性を有し、耐薬品
性が大きく、酸化によりエポキシ環やアルコールに容易
に誘導出来るポリアリル化合物を提供することである。[Problems to be Solved by the Invention] The present invention provides polyallyl compounds that have a high functional group density per unit weight, good curability, high chemical resistance, and can be easily converted into epoxy rings or alcohols by oxidation. The goal is to provide the following.
【０００４】0004
【課題を解決するための手段】上記課題は、一般式（１
）で表されるポリアリル化合物を開発することにより達
成された。
一般式（１）[Means for solving the problem] The above problem is solved by the general formula (1
) was achieved by developing a polyallyl compound represented by General formula (1)
【０００５】[0005]
【化２】[Case 2]
【０００６】本発明の化合物の具体例を以下に示す。ビ
ス（３，５−ジアリル−４−ヒドロキシフェニル）スル
ホン、２，２−ビス（３，５−ジアリル−４−ヒドロキ
シフェニル）プロパン、２，２−ビス（３，５−ジアリ
ル−４−ヒドロキシフェニル）ブタン、３，３−ビス（
３，５−ジアリル−４−ヒドロキシフェニル）ペンタン
、４，４−ビス（３，５−ジアリル−４−ヒドロキシフ
ェニル）−２−メチルペンタン、チオビス（３，５−ジ
アリル−４−ヒドロキシ）ベンゼン、１，１−ビス（３
，５−ジアリル−４−ヒドロキシフェニル）シクロヘキ
サン、１，１−ビス（３，５−ジアリル−４−ヒドロキ
シフェニル）−１−フェニルエタン、ビス（３，５−ジ
アリル−４−ヒドロキシフェニル）ジフェニルメタン、
１，１−ビス（３，５−ジアリル−４−ヒドロキシフェ
ニル）−１−Ｐ−フェニルフェニルエタン。Specific examples of the compounds of the present invention are shown below. Bis(3,5-diallyl-4-hydroxyphenyl)sulfone, 2,2-bis(3,5-diallyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-diallyl-4-hydroxyphenyl) ) Butane, 3,3-bis(
3,5-diallyl-4-hydroxyphenyl)pentane, 4,4-bis(3,5-diallyl-4-hydroxyphenyl)-2-methylpentane, thiobis(3,5-diallyl-4-hydroxy)benzene, 1,1-bis(3
, 5-diallyl-4-hydroxyphenyl)cyclohexane, 1,1-bis(3,5-diallyl-4-hydroxyphenyl)-1-phenylethane, bis(3,5-diallyl-4-hydroxyphenyl)diphenylmethane,
1,1-bis(3,5-diallyl-4-hydroxyphenyl)-1-P-phenylphenylethane.
【０００７】以下、本発明を実施例によって更に詳述す
るが本発明はこれらの実施例によって制限されるもので
はない。[0007] The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited to these Examples.
【０００８】[0008]
【実施例】実施例１
ビス（３，５−ジアリル−４−ヒドロキシフェニル）ス
ルホンの合成ビス（３−アリル−４−ヒドロキシフェニ
ル）スルホン０．１モル、炭酸カリウム０．２２モル、
Ｎ，Ｎ−ジメチルアセトアミド１００ｍｌをフラスコに
秤とる。７０℃に加熱し、アリルブロマイド０．２１モ
ルを滴下し５時間かき混ぜ続ける。反応液を水に注ぎ、
析出した結晶をメタノールで再結晶して、融点８７〜８
８℃のビス（３−アリル−４−アリルオキシフェニル）
スルホンを得た。得られた化合物を窒素雰囲気下で２０
０℃で６時間加熱し、メタノールで再結晶を行い、融点
１１５〜１１６℃の目的物を得た。[Example] Example 1 Synthesis of bis(3,5-diallyl-4-hydroxyphenyl)sulfone 0.1 mol of bis(3-allyl-4-hydroxyphenyl)sulfone, 0.22 mol of potassium carbonate,
Weigh 100 ml of N,N-dimethylacetamide into a flask. The mixture was heated to 70°C, 0.21 mol of allyl bromide was added dropwise, and stirring was continued for 5 hours. Pour the reaction solution into water,
The precipitated crystals were recrystallized with methanol to give a melting point of 87 to 8.
Bis(3-allyl-4-allyloxyphenyl) at 8°C
I got sulfone. The obtained compound was heated under nitrogen atmosphere for 20
The mixture was heated at 0°C for 6 hours and recrystallized with methanol to obtain the desired product having a melting point of 115-116°C.
【０００９】実施例２
２，２−ビス（３，５−ジアリル−４−ヒドロキシフェ
ニル）プロパンの合成２，２−ビス（３−アリル−４−
ヒドロキシフェニル）プロパン０．１モル、炭酸カリウ
ム０．２２モル、Ｎ，Ｎ−ジメチルアセトアミド１００
ｍｌをフラスコに秤とる。７０℃に加熱し、アリルブロ
マイド０．２１モルを滴下し５時間かき混ぜ続ける。反
応液を水に注ぎ、酢酸エチルで抽出し濃縮して、液状の
２，２−ビス（３−アリル−４−アリルオキシキシフェ
ニル）プロパンを得た。得られた化合物を窒素雰囲気下
で２００℃で６時間加熱し、反応液を酢酸エチル／ヘキ
サンを用いてカラム処理を行い、液状の２，２−ビス（
３，５−ジアリル−４−ヒドロキシフェニル）プロパン
を得た。化学構造の確認はＮＭＲにより行った。下記に
測定結果を示す。Example 2 Synthesis of 2,2-bis(3,5-diallyl-4-hydroxyphenyl)propane 2,2-bis(3-allyl-4-
Hydroxyphenyl)propane 0.1 mol, potassium carbonate 0.22 mol, N,N-dimethylacetamide 100
Weigh ml into a flask. The mixture was heated to 70°C, 0.21 mol of allyl bromide was added dropwise, and stirring was continued for 5 hours. The reaction solution was poured into water, extracted with ethyl acetate, and concentrated to obtain liquid 2,2-bis(3-allyl-4-allyloxyxyphenyl)propane. The obtained compound was heated at 200°C for 6 hours under a nitrogen atmosphere, and the reaction solution was subjected to column treatment using ethyl acetate/hexane to obtain liquid 2,2-bis(
3,5-diallyl-4-hydroxyphenyl)propane was obtained. The chemical structure was confirmed by NMR. The measurement results are shown below.
Claims (1)
式（１） 【化１】Claim 1: Polyallyl compound of general formula (1) General formula (1) [Chemical formula 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4970491A JPH04288031A (en) | 1991-03-14 | 1991-03-14 | Polyallyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4970491A JPH04288031A (en) | 1991-03-14 | 1991-03-14 | Polyallyl compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04288031A true JPH04288031A (en) | 1992-10-13 |
Family
ID=12838579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4970491A Pending JPH04288031A (en) | 1991-03-14 | 1991-03-14 | Polyallyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04288031A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000191575A (en) * | 1998-12-25 | 2000-07-11 | Kanegafuchi Chem Ind Co Ltd | Purification of bisphenol compounds, and bisphenol compounds produced by the purification |
| WO2001072678A1 (en) * | 2000-03-28 | 2001-10-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Phenol derivatives, process for preparation of the same and use thereof |
| JP2003104923A (en) * | 2002-08-29 | 2003-04-09 | Nippon Kayaku Co Ltd | Method for producing allylated polyhydric phenol compound |
| JP2007204635A (en) * | 2006-02-02 | 2007-08-16 | Nagase Chemtex Corp | New epoxy resin |
| JP2019048905A (en) * | 2017-09-07 | 2019-03-28 | 信越化学工業株式会社 | Resin composition, resin film, semiconductor laminate, method for producing semiconductor laminate and method for producing semiconductor device |
-
1991
- 1991-03-14 JP JP4970491A patent/JPH04288031A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000191575A (en) * | 1998-12-25 | 2000-07-11 | Kanegafuchi Chem Ind Co Ltd | Purification of bisphenol compounds, and bisphenol compounds produced by the purification |
| WO2001072678A1 (en) * | 2000-03-28 | 2001-10-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Phenol derivatives, process for preparation of the same and use thereof |
| JP2001342154A (en) * | 2000-03-28 | 2001-12-11 | Hayashibara Biochem Lab Inc | Phenol derivative, method for producing the same and use thereof |
| JP2003104923A (en) * | 2002-08-29 | 2003-04-09 | Nippon Kayaku Co Ltd | Method for producing allylated polyhydric phenol compound |
| JP2007204635A (en) * | 2006-02-02 | 2007-08-16 | Nagase Chemtex Corp | New epoxy resin |
| JP2019048905A (en) * | 2017-09-07 | 2019-03-28 | 信越化学工業株式会社 | Resin composition, resin film, semiconductor laminate, method for producing semiconductor laminate and method for producing semiconductor device |
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